Ammonia → HCID 22986586, compound

HRID 351969Notes

Reaction equation

HRID 351969 reaction equation
C([O:9][CH2:10][C@H:11]1[O:15][CH:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][C:19]([NH2:29])=[N:20][C:21]=3[NH:25][CH:26]2[CH2:28][CH2:27]2)[CH2:13][O:12]1)(=O)C1C=CC=CC=1.N>CO>[OH:9][CH2:10][C@H:11]1[O:15][CH:14]([N:16]2[CH:24]=[N:23][C:22]3[C:17]2=[N:18][C:19]([NH2:29])=[N:20][C:21]=3[NH:25][CH:26]2[CH2:28][CH2:27]2)[CH2:13][O:12]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22986581HCID 22986581, compound

Product 1

HCID 22986586HCID 22986586, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The starting material (Compound 24: 3.3 g) was stirred with ammonia in MeOH (80 mL; 2M) for 20 hrs. Nitrogen was bubbled through the reaction mixture to remove the excess ammonia. Then, the solution was concentrated to yield the crude as a β/α mixture (β/α=2.3:1). The β/α isomers were separated by chromatography on silica gel using DCM/MeOH as eluent to yield 1.18 g (70% β isomer).

Workup

  1. customNitrogen was bubbled through the reaction mixture
  2. customto remove the excess ammonia
  3. concentrationThen, the solution was concentrated
  4. customto yield the crude as a β/α mixture (β/α=2.3:1)
  5. customThe β/α isomers were separated by chromatography on silica gel
  6. customto yield 1.18 g (70% β isomer)

Sources & evidence

ORD record
ord-1595ca94c9f749788eb0c5322f0fa512
Source dataset
uspto-grants-2004_06
Patent number
US06743910B2

Reaction notes

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